Does Michael Moore hate America? That's a hard question to answer - he certainly hates America as it is. I doubt seriously if there ever was or ever will be the America the Left wants to reach or go back to. Michael Wilson is a young filmmaker who had a clever concept - turn Roger & Me on its head, and film himself trying to get an interview with Moore. The resulting movie, Michael Moore Hates America, didn't set the box office on fire, and it's not perfect, but it raises some good questions, and provides, for a change, some decent answers.
A few things need to be said up front. Mr. Wilson needed to drum up interest in the project, and he doubtless intended his title to be 'controversial', as he himself says in one of the many excellent snippets of an interview with documentarian Albert Mayles, a true legend (among his great films is the remarkable Gimme Shelter, the documentary of the Stone's '69 tour and its horrific culmination). The narration tends to be cloying at times, and despite the title, this is not (primarily) an expose of Moore so much as it is an affirmation that Americans are not the pathetic dupes that Moore seems to believe we are, but rather an optimistic people who know that into every life, a little rain must fall, but that just means you try harder.
The real heart of the movie is not Wilson's quest to get an interview with Moore, but two interviews that are excerpted heavily, one with the aforementioned Mayles, and one with Penn Jillette of the comedy/magic duo Penn & Teller. Jillette seems to think he's an extra in Goodfellas, so frequently does he drop the f-bomb, but he serves as one half of the movie's conscience, by discoursing on the techniques of propaganda, as used by Moore and others, and the false goal of catching 'reality' once a camera rolls (as anyone who's watched ten minutes of the execrable trend of 'reality' television can attest).
Mayles is the true anti-Moore, though, not in his politics (he makes it clear he liked Moore's notorious Oscar speech), but in his approach to the documentarian craft. Moore's 'documentaries' are anything but; instead, they are crafted set pieces that play to the faithful and confirm the prejudices already held by the filmmaker and his audience. The Mayles approach is different; to paraphrase his own words, he starts from the base of a love with his subject, but then he lets the chips fall where they may; the film is as honest as a documentary can be (given the parameters discussed by Jilette), and the conclusions are neither foregone nor telegraphed to the audience.
In fact, that is the Achilles' heel of Michael Moore Hates America. Wilson knew the kind of movie he wanted to make, and he set out making it (that's all well and good for a work of fiction, but as Mayles shows us, that's no way to make a documentary). To his credit, he lets the camera show things Moore would never show, including his own occasional deceptiveness towards his interview subjects. Moore, of course, looks like the complete jackass that he is throughout, and that's fun to watch. As you've no doubt surmised, it is the interview footage with Jillette and Mayles (and a fidgety David Horowitz) that provide the real reason to watch this flawed, but still quite interesting, labor of love.